Detainment is the most serious and impactful response to juvenile crime that a youth can experience (Pederson et al., 2020). Impacts of incarceration are long-lasting, and can include mental and physical health symptoms, relationship issues, and limited opportunities once released into the community, among others (Haney, 2003; Liebling & Maruna, 2013). These impacts are all the more pronounced in individuals who are detained in adolescence—a sensitive developmental period where ideas about self, others, and the world are rapidly forming and evolving (Erikson, 1950; Sanders, 2013; Steinberg & Morris, 2001). While existing research has explored these negative impacts of juvenile incarceration and the risk factors often preceding youth incarceration (Gatti et al., 2009; Jaffee et al., 2012), little is known about how individuals who experience juvenile incarceration have made meaning of their experience or how they have adapted and adjusted to life post-incarceration. Meaning making—finding one’s sense of purpose in the world and making sense of challenging events (Frankl, 2006; Park, 2010)—is a cornerstone of development during adolescence specifically and across the lifespan. The current study aims to explore the process of meaning making in formerly incarcerated adolescents and how this process evolves from before, during, and after incarceration. We utilized an online survey with the largest known sample of formerly incarcerated youth to date exploring meaning making and recovery from incarceration. This study utilized cluster analysis to identify unique trajectories of adaptation for this population to assess change over time. ANOVAs were used to determine which pre-incarceration variables predicted trajectory membership, and to see which post-incarceration outcome variables were predicted by trajectory membership. Results revealed five distinct recovery trajectories following pathways of adjustment from before, during, and after juvenile incarceration. Clusters were descriptively named: Consistent Low Satisfaction, New Perspective, Recovery, Consistent Moderate Satisfaction, and Consistent High Satisfaction. Clusters defined trajectories that differed in their initial (pre-incarceration) satisfaction with life (SWL) and also in terms of their changes in SWL over the three time points (pre-incarceration, incarceration, post-incarceration). Clusters 1 and 2 (Consistent Low Satisfaction, n = 23; New Perspective, n = 45) reflected very low initial SWL, which remained consistent over time for Cluster 1 but increased sharply at post-incarceration for Cluster 2. Clusters 3 and 4 (Recovery, n = 16; Consistent Moderate Satisfaction, n = 17) were characterized by moderate SWL pre-incarceration and showed somewhat different patterns of change over time, with Cluster 4 characterized by a drop in SWL during incarceration and a rebound post-release. Cluster 5 (Consistent High Satisfaction, n = 3) was viewed as a possibly anomalous cluster, because the small n for this cluster raises questions about replicability for this trajectory. The presence of meaning at Time 1 emerged as the only significant predictor of trajectory membership. Several outcome variables were uniquely predicted by trajectory membership. Meaning making emerged as an important factor in how individuals make sense of their lives and their carceral experiences. Demographic analyses revealed a potential confound may be perceived social class in childhood and in the present, as these variables differed significantly between clusters. These findings support the potential utility of focusing on meaning-making in treatment with justice-impacted youth and in individuals who have been released from incarceration. The crucial importance of accessible mental health treatment prior to, during, and following incarceration is discussed.